Hydrochloric Acid → HCID 178436792, compound

HRID 2254893Notes

Reaction equation

HRID 2254893 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:50][CH3:51])=[N:5][C:6]([CH2:48][CH3:49])=[CH:7][C:8]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[N:25]=[N:26][N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:28]=2)=[CH:14][CH:13]=1)[CH3:10]>CO>[Cl:2][C:3]1[C:4]([CH2:50][CH3:51])=[N:5][C:6]([CH2:48][CH3:49])=[CH:7][C:8]=1[N:9]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[NH:28][N:27]=[N:26][N:25]=2)=[CH:16][CH:17]=1)[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19742890HCID 19742890, compound

Product 1

HCID 178436792HCID 178436792, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.4 ml) was added to a suspension of 3-chloro-2,6-diethyl-4-[N-(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl-N-methylamino]pyridine (A) (220 mg) in methanol (5 ml) and the mixture was stirred for 6 hours. Volatile material was removed by evaporation and the residue partitioned between ether and sodium carbonate solution. The aqueous layer was separated, acidified to pH 6 with 4M hydrochloric acid and extracted with dichloromethane (3×25 ml). The combined organic extracts were dried and solvent removed by evaporation. The residue was purified by flash chromatography eluting with dichloromethane/methanol (9:1 v/v) to give 3-chloro-2,6-diethyl-4-[N-(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl-N-methylamino]pyridine as a solid, m.p. 110° C. (decomposition); NMR (d6 -DMSO): 1.1(d, of t, 6H), 2.64(q, 2H), 2.74(s, 3H), 2.84(q, 2H), 4.37(s, 2H), 6.81(s, 1H), 7.07(d, 2H), 7.27(d, 2H), 7.6(m, 4H); mass spectrum (+ve FAB, DMSO): 432,434(M+H)+ ; microanalysis, found: C, 64.6; H, 6.0; N, 17.9%; C24H25N6Cl.0.75H2O.0.125C4H10O requires: C, 64.4; H, 5.9; N, 18.4%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue partitioned between ether and sodium carbonate solution
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (3×25 ml)
  5. customThe combined organic extracts were dried
  6. customsolvent removed by evaporation
  7. customThe residue was purified by flash chromatography
  8. washeluting with dichloromethane/methanol (9:1 v/v)

Sources & evidence

ORD record
ord-26d36c76f7a744daa62740463c5975c7
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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